Self-Neutralizing Amino Acid Based Cationic Compositions

ABSTRACT

The invention described herein includes a self-neutralizing amino acid-based cationic composition that contains an amino acid-based cationic ester, a nonionic amphiphile, and an anhydrous buffering agent. In an embodiment, the composition, when dispersed or dissolved in an aqueous solvent, provides a resultant solution/dispersion having a pH of greater than about 4. The amino acid-based cationic ester may be a reaction product of (i) an amino acid having a non-polar side chain, and an amine group that has been neutralized with an acid; with (ii) a long chain fatty alcohol. Also included within the scope of the invention are methods of preparing a self-neutralizing amino acid-based cationic composition, such method including combining an amino acid-based cationic ester, a nonionic amphiphile and an anhydrous buffering agent. The resulting composition is in an anhydrous solid form. Formulations containing the amino acid-based cationic ester and/or a composition that includes it, are also disclosed.

CROSS REFERENCE TO RELATED APPLICATION

This application claims the benefit under 35 U.S.C. § 119(e) of U.S.Provisional Patent Application Ser. No. 62/815,314, filed Mar. 7, 2019,entitled, “Self-Neutralizing Amino-Acid Based Cationic Compositions,”the entire disclosure of which is incorporated herein by reference.

BACKGROUND OF THE INVENTION

Non-petrochemically derived cationic emulsifiers that are neutralizedamino acid esters are described and claimed in U.S. Pat. No. 8,105,569of Burgo and its related applications. These amino acid-based cationicesters (hereinafter “AABC”s) of Burgo may be supplied as an anhydrousform, i.e., a form that does not contain water in any significantquantity, e.g., less than about 5% water by weight.

The AABC compositions of Burgo are comprised predominantly of amino acidesters where the amino groups are neutralized by strong organic acids,e.g., ethanesulfonic acid (ESA), which renders the amino acid esterscationically charged species. The AABC compositions may also containminor quantities, e.g., <2 wt %, of unreacted amino acids, e.g.,isoleucine or valine, which are also neutralized by the strong organicacids to yield strongly acidic salts, e.g., isoleucine esylate or valineesylate.

When the AABC compositions of Burgo are dissolved or dispersed inaqueous media, they tend to yield aqueous compositions with rather lowpH values, e.g., pH <3.0. Without wishing to be bound by theory, it isbelieved that these low pH values are attributable to the fact that theAABC is the salt of a strong acid and a weak base. The anion, i.e., theconjugate base of the strong acid, will become a spectator ion and failto attract protons, while the cation from the weak base will donateprotons to the water forming hydronium ions (H₃O⁺), thus lowering thesolution pH value. Additionally, the strongly acidic amino acid salts,e.g., isoleucine esylate or valine esylate, present as unreactedbyproducts in the AABC composition, will also contribute to lowering thesolution pH.

Such low pH values are undesirable in many applications, especially inpersonal care and cosmetics, where most products are formulated at pH≥4.0. Previously, formulations prepared with AABCs thus required carefuland time-consuming adjustment of pH using suitable bases to achievestable pH values in the desired range. For example, typical values ofskin pH reported in the literature range from pH 4.5-pH 5.0, and this istypically a desired pH value associated with personal care products fortopical use on skin. See, e.g., J. W. Weichers, Formulating at pH 4-5:How Lower pH Benefits the Skin and Formulations, Cosmetics & Toiletries,2008, 123(12), 61-70.

There remains a need in the art for an amino acid-based cationic esterthat, when included in a formulation, provides a resultantsolution/dispersion having a pH suitable for personal care and cosmeticproducts.

BRIEF SUMMARY OF THE INVENTION

The invention described herein includes a self-neutralizing aminoacid-based cationic composition that contains an amino acid-basedcationic ester, a nonionic amphiphile, and an anhydrous buffering agent.In an embodiment, the composition, when dispersed or dissolved in anaqueous solvent, provides a resultant solution/dispersion having a pH ofgreater than about 4.

The amino acid-based cationic ester may be a reaction product of (i) anamino acid having a non-polar side chain, and an amine group that hasbeen neutralized with an acid; with (ii) a long chain fatty alcohol.

Also included within the scope of the invention are methods of preparinga self-neutralizing amino acid-based cationic composition, such methodincluding combining an amino acid-based cationic ester, a nonionicamphiphile and an anhydrous buffering agent. The resulting compositionis in an anhydrous solid form.

Formulations containing the amino acid-based cationic ester and/or acomposition that includes it, are also disclosed.

BRIEF DESCRIPTION OF THE SEVERAL VIEWS OF THE DRAWING

The foregoing summary, as well as the following detailed description ofpreferred embodiments of the invention, may be better understood whenread in conjunction with the appended drawings.

The invention is not limited to the precise arrangements andinstrumentalities shown. In the drawings:

FIG. 1 shows the pH of aqueous compositions as a function of wt % AABCblend in the composition of Examples 4 to 6 and Comparative Examples 4to 6;

FIG. 2 is a polarized light micrograph (400× magnification) of anexemplary formulation of the invention that includes 15% of theself-neutralizing AABC composition prepared in accordance with theinvention;

FIG. 3 show SAXS data for lamellar LC systems comprising brassicylvalinate esylate; and

FIG. 4 show SAXS data for lamellar LC systems comprising brassicylisoleucinate esylate.

DETAILED DESCRIPTION OF THE INVENTION

The present invention provides a self-neutralizing amino acid-basedcationic composition that can be dissolved or dispersed in water toprovide an aqueous composition having a desirable pH value (about 3.5 toabout 7) eliminating the need for pH adjustment via addition of base.The present invention also provides methods for preparingself-neutralizing amino acid-based cationic compositions and methods forpreparing compositions comprising self-neutralizing amino acid-basedcationic compositions.

The self-neutralizing amino acid-based cationic compositions asdescribed herein include an amino acid-based cationic ester, i.e., aneutralized amino acid ester, a nonionic amphiphile and an anhydrousbuffering agent (hereinafter “ABA”). Each component may be independentlypresent in the composition in singular form (e.g., one type of aminoacid-based cationic) or as a mixture (e.g., a mixture of two or moreamino acid-based cationic esters). Details of the individual componentsof the composition are provided below. When dispersed or dissolved in anaqueous solvent such as water, the resultant solution/dispersion has apH of greater than about 3.5, about 3.5 to about 7, about 4 to about6.5, about 4 to about 5.5, or about 4 to about 5.

For use in the self-neutralizing AABC composition as described herein,one may use the neutralized amino acid ester (i.e., the amino acid-basedcationic ester) (hereinafter “AABC”) as described in Burgo. The contentsof Burgo are imported herein by reference, and which is provided forconvenience at Appendix A. In general, such AABC may be prepared fromthe esterification of (i) an amino acid having a non-polar side chainwherein the amine group of the amino acid has been neutralized with anacid; with (ii) a long chain fatty alcohol. The AABC may represented bythe structure of formula (I):

In (I), R¹ represents an alkyl group, which may be branched or linear.It may have one to ten carbon atoms or two to six carbon atoms. R²represents a carbon chain that may be linear or branched. It may containten to fifty carbon atoms or twenty-four to thirty-two carbon atoms. Thechain of R² may contain at least one unsaturated carbon atom. In anembodiment, R² is an alkyl group having eight to twenty-four carbonatoms. X⁻ represents the conjugate base of the acid used to neutralizethe amino acids ester.

Amino acids for the formation of the AABC include any that are neutral.In an embodiment, one may select L-alanine, L-valine, L-leucine andL-isoleucine. Particularly preferred, in some embodiments of theinvention, are L-isoleucine and L-valine. Other options may include anyα,ω-aminoalkylcarboxylic acid, e.g., 11-aminoundecanoic acid or12-aminododecanoic acid.

To obtain the ester of the invention, the amine group of the amino acidis neutralized with an acid and is reacted with a long chain fattyalcohol. Suitable fatty alcohols may be linear and/or branched and mayadditionally be saturated and/or unsaturated. It may be preferred thatthe fatty alcohol contains about ten to about fifty or about twenty-fourto about thirty-two carbon atoms. In an embodiment, linear and/orbranched fatty alcohols containing from about twelve to about twenty-twocarbon atoms may be preferred. In another embodiment, linear fattyalcohols containing about sixteen to about twenty-four carbon atoms arepreferred.

Examples of suitable fatty alcohols include lauryl alcohol, myristylalcohol, palmityl alcohol, stearyl alcohol, oleyl alcohol, isostearylalcohol, arachidyl alcohol, behenyl alcohol and mixtures or combinationsthereof. It is advisable that the fatty alcohols are derived fromnon-petrochemical sources. In an embodiment, the AABC is a reactionproduct of the amino acid and the fatty alcohol, where the amino acid isL-alanine, L-valine, L-leucine, L-isoleucine, and/or mixtures of thesame, and the fatty acid is coconut oil (including mixture of variouslong chain fatty acids), stearyl alcohol, isostearyl alcohol, and/orbrassicyl alcohol (optionally hydrogenated). Brassica alcohol, as usedherein, is defined as the fatty alcohol produced from the seed oilsderived from plants of the family Brassicaceae containing or primarilycontaining C₁₈, C₂₀, and C₂₂ fatty alcohols.

In some embodiments it may be preferred that AABC a fatty alcohol esterwith the amino acid being L-valine or L-isoleucine, neutralized withethanesulfonic acid and which is preferably solid at 25° C. Such AABCsmay include, for example, brassicyl valinate esylate, cetyl valinateesylate, cetearyl valinate esylate, stearyl valinate esylate, isostearylvalinate esylate, behenyl valinate esylate, octyldodecyl valinateesylate, decyltetradecyl valinate esylate; brassicyl isoleucinateesylate, cetyl isoleucinate esylate, cetearyl isoleucinate esylate,stearyl isoleucinate esylate, isostearyl isoleucinate esylate, behenylisoleucinate esylate, octyldodecyl isoleucinate esylate, decyltetradecylisoleucinate esylate; most preferably brassicyl valinate esylate and/orbrassicyl isoleucinate esylate.

AABC may be synthesized by any methods known or developed in the art.However, illustrative examples of synthesis are provided in Burgo andare incorporated herein by this reference.

The composition also includes at least one nonionic amphiphile; it maybe preferred that the selected nonionic amphiphile is one that is asolid 25° C. It may, in some embodiments, contain about 10 to about 35carbon atoms, about 15 to about 30 carbon atoms and about 16 to about 24carbon atoms. Exemplary nonionic amphiphiles may include:

Fatty alcohols, such as, for example, straight chain or branched fattyalcohol comprising 12 or more carbon atoms, including, for example,lauryl, myristyl, cetyl, cetearyl, stearyl, isostearyl, oleyl,arachidyl, behenyl, octyldodecyl, decyltetradecyl, coconut alcohol, palmalcohol, palm kernel alcohol, brassica alcohol, hydrogenated rapeseedalcohol; preferably linear fatty alcohol comprising 16 or more carbonatoms; most preferably brassica, cetyl, cetearyl, stearyl, or behenyl;

Fatty glyceryl esters, such as, for example, mono-, di-, or triester ofglycerol or mixtures thereof that include esters of glycerol and one ormore fatty acids comprising 12 or more carbon atoms, such as, forexample, glyceryl laurate, glyceryl myristate, glyceryl palmate,glyceryl sesquistearate, glyceryl stearate, glyceryl stearate se,glyceryl behenate, glyceryl distearate, brassica glycerides,hydrogenated rapeseed glycerides, hydrogenated coco-glycerides,hydrogenated C₁₂₋₁₈ glycerides, hydrogenated palm glycerides,hydrogenated soy glycerides; preferably brassica glycerides;

Fatty glycol esters, such as, for example, mono- or diester of ethyleneglycol or mixtures thereof; esters of ethylene glycol and one or morefatty acids comprising 12 or more carbon atoms, such as, glycolstearate, glycol distearate, glycol behenate, glycol dibehenate;

Fatty esters of polyglycerol, such as, for example, polyglyceryl estersare monoacyl or polyacyl esters (e.g., bearing an average of 1.5 to 10ester groups per polyglyceryl chain) of polyglycerols having an averagedegree of polymerization of 2 to 10 glyceryl repeat units and having anacyl group of about 12 to about 24 carbon atoms, where acyl groups mayinclude lauroyl, cocoyl, myristoyl, palmitoyl, stearoyl, arachidonoyl,behenoyl, and brassicoyl, such as, for example, polyglyceryl-3 stearate,polyglyceryl-3 stearate SE, polyglyceryl-4 stearate, polyglyceryl-10stearate, polyglyceryl-6 sesquistearate, polyglyceryl-4 pentastearate,polyglyceryl-6 pentastearate, polyglyceryl-10 pentastearatepolygyceryl-3 behenate, polyglyceryl-5 tribehenate, polyglyceryl-6tetrabehenate, polyglyceryl-2 distearate, polyglyceryl-3 distearate,polyglyceryl-6 distearate, polyglyceryl-10 distearate, polyglyceryl-2palmitate, polyglyceryl-3 palmitate, polyglyceryl-4 palmitate,polyglyceryl-6 palmitate, polyglyceryl-6 dipalmitate, polyglyceryl-4laurate, polyglyceryl-5 laurate, polyglyceryl-6 laurate, polyglyceryl-7laurate, polyglyceryl-8 laurate, polyglyceryl-10 laurate, polyglyceryl-2myristate, polyglyceryl-3 myristate, polyglyceryl-4 myristate,polyglyceryl-5 myristate, polyglyceryl-6 myristate, polyglyceryl-10myristate, and polyglyceryl-5 pentamyristate;

Fatty esters of methyl glucose such as, for example, methyl glucoseesters like monoacyl or polyacyl esters (e.g., bearing an average of 1.5to 3 ester groups per methyl glucose unit) of methyl glucose when anacyl group of about 12 to about 24 carbon atoms, where the acyl groupsmay include lauroyl, cocoyl, myristoyl, palmitoyl, stearoyl,arachidonoyl, behenoyl, and brassicoyl, such as, for example, methylglucose dioleate, methyl glucose isostearate, methyl glucose laurate,methyl glucose sesquicaprylate/sesquicaprate, methyl glucosesesquicocoate, methyl glucose sesquiisostearate, methyl glucosesesquilaurate, methyl glucose sesquioleate, and methyl glucosesesquistearate;

Fatty esters of sorbitan, such as, for example, monoacyl or polyacylesters (e.g., bearing an average of 1.5 to 4 ester groups per methylglucose unit) of sorbitan and having an acyl group of about 12 to about24 carbon atoms, including, for example, lauroyl, cocoyl, myristoyl,palmitoyl, stearoyl, arachidonoyl, behenoyl, and brassicoyl Examplesinclude sorbitan cocoate, sorbitan dioleate, sorbitan distearate,sorbitan laurate, sorbitan oleate, sorbitan olivate, sorbitan palmitate,sorbitan palmate, sorbitan sesquioleate, sorbtian sesquisteatate,sorbitan stearate, sorbitan trioleate, and sorbitan tristearate.

The composition further includes an anhydrous buffering agent (“ABA”).By describing a material herein, such as the buffering agent, as“anhydrous” it is meant that the material is substantially free of addedwater, preferably containing less than about 5% water, more preferablyless than about 4% water, even more preferably less than about 2% water,and most preferably less than about 1.5% water. Anhydrous materials maycontain minor amounts of incidental water, e.g., from absorption ofambient humidity or processing conditions, e.g., washing followed byincomplete drying). In some embodiments, it is preferred that the ABA isin a particulate form or a powder form, for example, it is a finelydivided solid having a small particle size, preferably less than about100 μm.

ABAs suitable for use in the inventive composition include any known orto be developed in the art or combinations of the same. In variousembodiments, the ABA is a material capable of maintaining the pH of theaqueous solution when the AABC composition is dissolved in water.

If in a powder form, the ABA may be a free-flowing solid with averageparticle size of less than about 100 μm, preferably less than about 75μm, more preferably less than about 50 μm, even more preferably lessthan about 25 μm, in certain embodiments, the average particle size willbe less than about 20 μm. In many embodiments, a powder form of smallparticle size may be used to facilitate the maintenance of uniformdispersion of the ABA throughout the composition during processing inthe molten state and during the process of cooling and solidification toyield a solid form with buffering agent dispersed homogeneouslythroughout.

In various embodiments, the ABA selected may be a salt of a strong baseand a weak organic acid, e.g., where strong base is sodium hydroxide,potassium hydroxide, calcium hydroxide and the like, and the weak acidis gluconic acid, citric acid, lactic acid, and the like.

Exemplary ABAs for use in the composition of the invention include, forexample, alkali metals or alkaline earth metal salts of gluconic acid,e.g., sodium gluconate, calcium gluconate.

As prepared, the composition of the invention may contain any of thetwo/three above-described components in any relative quantity; suchrelative quantities may vary depending on several factors, including,for example, manufacturing parameters, the contemplated end use of thecomposition, and the like as is appreciated in the art. Thus, thevariation of the relative quantities is a matter of routine by a personof skill in the art.

For illustration of the invention, however, it is suggested that theAABC is present in the composition in an amount of about 10 wt % toabout 70 wt %, about 12 wt % to about 60 wt %, about 15 wt % to about 55wt %, or about 20 wt % to about 50 wt %, each with reference to theweight of the total composition.

In some embodiments, one may include the ABA in the composition in theamounts of about 2 wt % to about 25 wt %, about 4 wt % to about 20 wt %,about 6 wt % to about 15 wt %, or about 8 wt % to about 12 wt %, eachwith reference to the weight of the total composition.

In many embodiments, the balance of the composition may be made up ofthe selected nonionic amphiphile(s). If other ingredients at included inthe composition of the invention, the selected nonionic amphiphile(s)may be present in amount of at least about 10 wt %, about 15 wt % toabout 70 wt %, in some embodiments preferably about 20 wt % to about 40wt %, each with reference to the total composition.

In various embodiments, regardless of the amount of nonionic amphiphilepresent, the ratio of AABC to ABA in the composition may be: (i) on aweight basis (wt %:wt %): about 1:2 to about 1:8, about 1:2 to about1:6, about 1:2 to about 1:4, or about 1:2 to 1:3; or (ii) on a molarbasis: about 1:1 to about 1:5, about 1:1 to about 1:4, about 1:1 toabout 1:3, or about 1:1 to about 1:2. In some embodiments, the molarratio of AABC to anhydrous buffering agent may be 1:1 or 1:2.

The composition is, in many embodiments, in an anhydrous form,preferably an anhydrous solid form.

The self-neutralizing AABC compositions may include other ingredients.Such ingredients are preferably in a powder form and/or are alsoanhydrous. Examples include water-soluble polymers or gums, such as guarhydroxypropyltrimonium chloride, hydroxypropyl guar, polyquaternium-10,hydroxyethyl cellulose, hydroxypropylmethyl cellulose, starch, guar gum,cassia gum, and the like; chelating agents, such as tetrasodium EDTA,disodium EDTA, tetrasodium glutamate diacetate, and the like; andzwitterionic surfactants, such as cocamidopropyl betaine, cocamidopropylhydroxysultaine, lauramidopropyl betaine, and the like.

The self-neutralizing AABC compositions may also contain other solid orsemi-solid ingredients that are capable of being incorporated into thecomposition in the molten phase, such as, for example, plant derivedtriglycerides, i.e., oils and butters, and waxes and wax esters,preferably nonpetrochemically derived. Other therapeutic or cosmeticbenefit agents including antioxidants, such as tocopheryl acetate orascorbyl palmitate may also be added to the self-neutralizing AABCcompositions.

The self-neutralizing AABC compositions of the invention may be preparedby any process known or developed in the art. However, for illustrativepurposes, a general process of manufacture is as follows: the AABC andnonionic amphiphiles are heated until completely melted and mixed toform a homogenous molten mixture. The anhydrous buffering agent isdispersed in the molten mixture to produce a uniform dispersion of thepowder in the molten mixture, preferably under shear. This dispersion ismaintained under heat and shear during processing to ensure it remainshomogeneous while in the molten state.

In an embodiment, care should be taken to ensure that the ABA does notsettle out, e.g., via sedimentation, during processing. A homogeneousmixture may be maintained by applying constant shear, e.g., with amechanical mixer. In larger vessels, recirculation of the contents viapumping and in-line shear mixing may be combined with mechanical mixingto maintain a homogeneous dispersion of the ABA in the molten mixture.

The molten mixture is then cooled. If desired a solid may be achieved toincrease convenience of subsequent post-manufacture handling andprocessing, if such is desired. In some embodiments, the composition maybe subject to various post manufacture processes, such as for example,flaking, pastillation, prilling, beading, extrusion and pelletizing,etc. For example, the mixture can be spread in a thin layer on a chilledsurface and allowed to cool and solidify; the resulting solid sheet canbe broken into small pieces (flakes) and stored for subsequentcompounding into formulations. The cooling and solidification processesare preferentially configured to ensure that a uniform homogeneousdistribution of buffering agent is present in the solid form, e.g., fromflake to flake or pastille to pastille, and from the beginning of a runto the end of a run when conducted on large scale continuously operatingequipment; therefore, cooling and solidification must occur on a timescale that is much faster than the settling rate (i.e., sedimentationvelocity) of the ABA particulate in the molten mixture.

The compositions of the invention may be incorporated into many consumerand industrial end formulations, for example, formulations for personalcare, home & institutional care, pharmaceutical, veterinary care, oralcare, textile care, metalworking, food processing, and industrialapplications.

In an embodiment of the invention, the composition is incorporated withat least one other ingredient to form a formulation such as a personalcare formulation. Suitable additive ingredients include water,surfactants, emollients, humectants, conditioning agents for hair, skinor nails, chelating agents, active agents, beaching or whitening agents,additional pH adjusting agents, fragrances, colorants, exfoliatingagents, antioxidants, botanical ingredients, e.g., plant extracts, mica,smectite, thickeners, pharmaceuticals, cannabinoids, oils, dyes, waxes,amino acids, nucleic acids, vitamins, hydrolyzed proteins andderivatives thereof, glycerine and derivates thereof, enzymes,anti-inflammatory and other medicaments, microbiocides, antifungals,antiseptics, antioxidants, UV absorbers, dyes and pigments,preservatives, sunscreen active agents, sweat retardants, oxidizers, pHbalancing agents, glyceryl monoesters, moisturizers, peptides andderivatives thereof, anti-aging actives, hair growth promoters,anti-cellulite actives and the like acceptable for use in formulationsfor human use.

Such formulations may have end use as, for example without limitation, aconditioner of hair, nails, skin or textile, shampoo, hair spray,mustache/beard oils or waxes, hair-styling preparation, permanent waveliquids, hair colorant, glaze, skin lotion, face & body wash, makeupremover, cleansing lotion, emollient lotion/cream. bar soap, shavingcreams, sunscreen, sunburn treatment, deodorants, moisture gel, moistureessence, UV exposure-preventing essence, shaving foam, face powder,foundation, lipstick, blush, eyeliner, wrinkle and anti-aging cream, eyeshadow, eyebrow pencils, mascara, mouthwash, toothpaste, an oral carecomposition, a skin cleansing composition, a textile cleansingcompositions, a dish cleaning composition, a hair or fur cleansingcomposition, a deodorant or antiperspirant, a cosmetic, a hair stylingcomposition, a skin moisturizer, a skin conditioner, a hair conditionerand a nail conditioner.

These formulations including the self-neutralizing AABC compositions ofthe invention may be prepared by any process known or developed in theart. However, for illustrative purposes, a general process is asfollows: A water phase is heated to a temperature above the meltingtemperature of the self-neutralizing AABC composition and maintainedunder shear (mixing). While mixing, the solid self-neutralizing AABCcomposition is slowly added and allowed to disperse and melt into thewater phase. The formulation is mixed until the buffering agent of theAABC is dissolved and a stable, uniform pH value is obtained throughoutthe resulting composition. Other ingredients may be added as appropriateeither before or after addition of the self-neutralizing AABCcomposition

As alternative process is as follows: The self-neutralizing AABCcomposition is heated to form a liquid; the liquid is maintained undershear (mixing) to ensure homogenous distribution of the buffering agent.A water phase is heated to about the same temperature as the moltenself-neutralizing AABC composition. The molten self-neutralizing AABCcomposition is combined with the heated water phase while heating andmixing; proper agitation is employed to ensure uniform mixing of the twophases. The formulation is mixed until the buffering agent of the AABCis dissolved and a stable, uniform pH value is obtained throughout theresulting composition. In this process, other ingredients may be addedas appropriate to either the water phase or the molten self-neutralizingAABC phase before the combination of the two phases, or to the resultingcomposition after the two phases have been combined.

For example, fatty alcohols, fatty acids, triglycerides, waxes, cosmeticoils, etc., may be mixed with the molten prior to combination with thewater phase. Alternatively, water-soluble ingredients, such ashumectants, chelating agents, viscosity increasing agents, e.g.,water-soluble polymers, and the like, may be added to the water phaseprior to combination with the molten self-neutralizing AABC phase.

In many embodiments, aqueous formulations prepared using theself-neutralizing AABC composition of the present invention will exhibitlamellar liquid crystalline (LC) phase behavior. Such LC phase behavioris readily characterized using techniques familiar to those skilled inthe art, such as polarized light microscopy, small-angle X-rayscattering (SAXS), and cryo freeze-fracture scanning electron microscopy(cryo-SEM). Lamellar LC systems may be characterized by the spacing ofthe lamellar bilayer sheets, known as the D-spacing. The lamellar LCphases formed by the compositions of the present invention may haveD-spacings as measured by SAXS from about 1 to about 100 nm, withcertain embodiments having D-spacings from about 2 nm to about 25 nm,and preferred embodiments having D-spacings from about 3 nm to about 15nm.

Those skilled in the art will recognize that the D-spacing of thelamellar LC phases can be modulated by altering one or more variables,including the carbon chain lengths of the AABCs and/or the nonionicamphiphiles in the self-neutralizing AABC composition, the levels ofAABC and nonionic amphiphiles in the formulation, or the ratio of AABCto nonionic amphiphile(s) in either the self-neutralizing AABCcomposition or in the formulation itself, e.g., additional AABC ornonionic amphiphile maybe be added to the formulation comprising theself-neutralizing AABC composition to affect the D-spacing of thelamellar LC phase. The pH, ionic strength, or level of dispersed oilphase in the formulation may also be varied to influence lamellarD-spacing. The lamellar LC phases of the present invention preferablyhave D-spacings that remain constant over the temperature range of20-60° C.

In another illustrative embodiment of a method of preparing aformulation in solid format that contains the self-neutralizingcompositions of the invention, the self-neutralizing AABC is heated to amolten state and mixed with appropriate agitation to maintain uniformdistribution of the buffering agent in the mixture. Additionalingredients are added and mixed into the molten mixture. The mixture iscooled to yield a solid formulation that exhibits a pre-selected pHvalue upon use by the end consumer.

For example, a 10% solution of the solid formulation will preferablyhave a pH value of about 3.5-about 6.5, more preferably about 3.7-about6.0, even more preferably about 3.8-about 5.5, and most preferably about3.8-about 5.0. The solid formulation maybe further processed viamilling, extrusion, or other processes to incorporate additionalingredients such as surfactants, conditioning agents, fragrances,colors, exfoliating agents, or other cosmetic or therapeutic benefitagents. The solid formulation may be fabricated into a variety of formssuch as bars, balls, sticks, and the like, by melting, casting intomolds and allowing to solidify, or via extrusion and stamping with apress into a molded shape.

EXAMPLES Examples 1 to 3 and Comparative Examples 1 to 3

The relative amounts of each ingredient used in Examples 1 to 3 andComparative Examples 1 to 3 are shown below in Table 1:

TABLE 1 Formula Wt % (as supplied) Comp Comp Comp Example ExampleExample Example Example Example INCI Name 1 1 2 2 3 3 Brassicyl 27.227.2 — — 31.4 31.4 Valinate Esylate* Brassicyl — — 36.0 36.0 — —Isoleucinate Esylate (Brassica Alcohol)** Brassica 63.3 72.8 54.4 64.028.8 34.3 Alcohol*** Brassica — — — — 28.8 34.3 Glycerides Calcium 9.5 —9.6 — 11.0 — Gluconate (anhydrous)^(∧) Total 100.0 100.0 100.0 100.0100.0 100.0 *Obtained from INOLEX, Inc., as AminoSensyl AS94 **Obtainedfrom INOLEX, Inc. as Emulsense ***Obtained from INOLEX, Inc. as SustOleoBA ****Obtained from INOLEX, Inc. as SustOleo BG ^(∧)Obtained fromSpectrum Chemical Products, New Brunswick, New Jersey.

Example 1—Procedure to Prepare a Self-Neutralizing AABC CompositionUsing Brassicyl Valinate Esylate

Brassicyl valinate esylate (BVE) and brassica alcohol (BA) were chargedto an appropriately sized beaker equipped with overhead mechanicalstirrer and propeller blade and hotplate for heating. The mixture wasgently heated while manually stirring with spatula to melt the solidingredients; upon liquefication, mixing at medium-high speed was startedand the temperature brought to 75-80° C. Anhydrous calcium gluconate(CaG) powder having a D50 average particle size of 11 μm was slowlysifted into the molten BVE/BA blend and mixed until uniformly dispersed.Immediately upon stopping stirring, the mixture was poured onto astainless steel tray, spread into a uniform thin layer, and allowed tocool to ambient temperature and solidify.

The solidified layer was scrapped off the tray to yield the flakes ofthe self-neutralizing AABC composition.

Comparative Example 1

The amounts in Table 1 and the procedure of Example 1 were used toprepare a comparative AABC composition. However, the calcium gluconatewas omitted from the composition in this example. Note that when the ABAis omitted from the AABC composition, additional nonionic amphiphile isadded in q.s. in the example to achieve 100 wt %.

Example 2—Procedure to Prepare Self-Neutralizing AABC Composition UsingBrassicyl Isoleucinate Esylate

The amounts in Table 1 and the procedure of Example 1 were used toprepare an AABC composition. However, in Example 2, the ABC wasbrassicyl isoleucinate esylate.

Comparative Example 2

The amounts in Table 1 and the procedure of Example 1 were used toprepare a comparative AABC composition. However, the calcium gluconatewas omitted from the composition in this example.

Example 3—Procedure to Prepare a Self-Neutralizing AABC Composition witha Secondary Nonionic Amphiphile

The amounts in Table 1 and the procedure of Example 1 were used toprepare a self-neutralizing AABC composition. However, in Example 3, theAABC was brassicyl valinate esylate and a secondary nonionic amphiphile,brassica glyceride, was added to the composition.

Comparative Example 3

The amounts in Table 1 and procedure of Example 1 were used to prepare acomparative AABC composition. However, the calcium gluconate was omittedfrom the composition in this example.

Examples 4 to 6 and Comparative Examples 4 to 6

The relative amounts of each ingredient used in Examples 4 to 6 andComparative Examples 4 to are the same as those used in Examples 1 to 3and Comparative Examples 1 to 3 (see Table 1). The pH data collected foreach are shown below in Table 2:

TABLE 2 pH value Comp Comp Comp Example Example Example Example 4 (usingExample 5 (using Example 6 (using Wt % 4 (Using Comp 5 (using Comp 6(using Comp AABC Example Example Example Example Example ExampleComposition 1) 1) 2) 2) 3) 3)  5 4.25 3.02 4.37 3.12 4.01 2.76 10 4.332.85 4.46 3.01 4.12 2.57 15 4.36 2.68 4.43 2.9 4.23 2.42 20 4.27 2.554.35 2.77 4.22 2.32

Example 4—Preparation of a Formulation Including Self-Neutralizing AABCComposition

A formulation was prepared as follows: To a beaker equipped withoverhead mechanical stirrer and propeller blade and hotplate for heatingwas charged deionized water (q.s. to 100 wt %), which was heated to75-80° C. The Aself-neutralizing ABC composition of Example 1 in thespecified amount (shown in Table 2) was slowly added to the hot waterphase while mixing at medium speed and mixed until completely anduniformly dispersed. The mixture was allowed to cool to ambienttemperature while mixing as low-medium speed and was then discharged toa container for storage. The formulation was allowed to equilibrateovernight and then the pH was measured using a pH meter. Thecompositions of Examples 4 to 6 including the self-neutralizing AABCcomposition were characterized using polarized light microscopy andobserved to exhibit lamellar LC phase behavior, as evidenced by thecharacteristic Maltese cross pattern.

FIG. 2 is a polarized light micrograph (400× magnification) of theExample 4 formulation comprising 15% of the self-neutralizing AABCcomposition of Example 1.

The compositions of Examples 4 and 5 comprising 15% of theself-neutralizing AABC composition were analyzed via SAXS tocharacterize the D-spacings of the resulting lamellar LC systems overthe temperature range of 20-70° C. FIGS. 3 and 4 show SAXS data forlamellar LC systems comprising brassicyl valinate esylate and brassicylisoleucinate esylate, respectively. The peaks observed are indicative ofD-spacings of 75 Å (7.5 nm) and 77 Å (7.7 nm) for the respectiveformulations. Disappearance of the peaks at temperatures exceeding 60°C. is indicative of a phase change to a nonlamellar system.

Comparative Example 4

The process of Example 3 was repeated using the material prepared inComparative Example 1 in the amount specified in Table 2.

Example 5—Preparation of a Formulation Including the Self-NeutralizingAABC Composition

The process of Example 4 was repeated using the self-neutralizing AABCcomposition prepared in Example 2 in the amount specified in Table 2.

Comparative Example 5

The process of Example 4 was repeated using the material prepared inComparative Example 2 in the amount specified in Table 2.

Example 6—Preparation of a Formulation Including a Self-NeutralizingAABC Composition

The process of Example 4 was repeated using the self-neutralizing AABCcomposition prepared in Example 3 in the amount specified in Table 2.

Comparative Example 6

The process of Example 4 was repeated using the material prepared inComparative Example 3 in the amount specified in Table 2.

The pH data collected from these examples is shown in FIG. 1. The dataof Table 2 and FIG. 1 demonstrate the pH buffering benefits of theself-neutralizing AABC compositions (Examples 1 to 3) when dispersed inwater.

As can be seen, aqueous compositions comprising Examples 1, 2, and/or 3demonstrate nearly constant pH values of 4.3-4.5 at concentrationsranging from 5 wt % to 20 wt % of AABC blend, whereas the comparativeexamples without the buffering agent (Comparative Examples 1, 2, and 3)exhibit lower pH values which decrease as a function of increasing AABCblend concentration.

Thus, the self-neutralizing AABC compositions of Examples 1, 2, and 3provide the benefit of a pH value appropriate for the formulation ofcomposition for hair care and skin care that is independent of use leveland does not require further adjustment upon compounding in aqueousmedia.

Example 7—Natural Rinse-Off Hair Conditioner

Table 3 shows the relative amounts of ingredients used in the followingexemplary formulation of a hair conditioner.

TABLE 3 Ingredient Trade Name Formula Wt % (INCI) (Supplier) (assupplied) Water Purified Water 84.53 Caprylhydroxamic Acid (and) Zeastat2.00 Propanediol (INOLEX) Brassica Alcohol (and) Example 1 10.22Brassicyl Valinate (INOLEX) Esylate (and) Calcium Gluconate BrassicaSustOleo BA 0.75 Alcohol (INOLEX) Triheptanoin SustOleo MCT 1.50(INOLEX) Diheptyl Succinate (and) LexFeel N350 0.75 Capryloyl Glycerin/(INOLEX) Sebacic Acid Copolymer Argania Spinosa (Argan) Argan Oil 0.25Kernel Oil 100.00

To an appropriately sized beaker equipped with overhead mechanicalstirrer and propeller blade and hotplate for heating was charged waterand caprylhydroxamic acid (and) propanediol, which was heated to 75-80°C. while mixing at low-medium speed. At 70-75° C., the self-neutralizingAABC blend of Example 1, brassica alcohol, triheptanoin, diheptylsuccinate (and) capryloyl glycerin sebacic acid copolymer, and Arganiaspinosa (argan) kernel oil were charged to the beaker.

The temperature was brought to 80-85° C. and the mixture was stirred for10-15 minutes at medium-high speed. Heating was stopped and the mixturewas allowed to cool to 70° C. while stirring at medium-high speed. At70° C., the mixture was homogenized for three minutes at high speed, andthen allowed to cool to 45 to 50° C. while stirring at slow speed withan anchor-type blade. At 50° C. the mixture was discharged to anappropriate container for storage. The pH of the resulting formulationwas 4.20 and the Brookfield viscosity (RVT (D), helipath spindle T-C, 10rpm) was 53,500 cP at room temperature (about 21° C.).

Example 8—Natural Leave-in Split End Mender

Table 4 shows the relative amounts of ingredients used in the followingexemplary formulation of a hair spilt end mender.

TABLE 4 Ingredient Trade Name Formula Wt % (INCI) (Supplier) (assupplied) Oil Phase Cetyl Alcohol Cetyl Alcohol, 5.00 NF DiheptylSuccinate (and) LexFeel N5 5.00 Capryloyl Glycerin/ (INOLEX) SebacicAcid Copolymer Brassica Alcohol (and) Example 1 12.50 Brassicyl Valinate(INOLEX) Esylate (and) Calcium Gluconate Cocos Nucifera (Coconut) OilVirgin Coconut 10.00 Oil (Anjou) Water Phase Water Purified Water 61.50Caprylhydroxamic Acid (and) Benzostat 1.00 Benzyl Alcohol (and) (INOLEX)Glycerin Glycerin Glycerin, USP 5.00 100.00

To an appropriately sized beaker equipped with overhead mechanicalstirrer and propeller blade and hotplate for heating was charged water,caprylhydroxamic acid (and) benzyl alcohol (and) glycerin, and glycerin.Mixing was started at low-medium speed and the mixture was heated to 80°C. In a separate beaker, cetyl alcohol, diheptyl succinate (and)capryloyl glycerin sebacic acid copolymer, the self-neutralizing AABCcomposition of Example 1, and Cocos nucifera (coconut) oil were combinedand heated to 80° C. while mixing and mixed until uniform.

The oil phase mixture was added to the water phase mixture at 80° C.while mixing at medium-high speed. The mixture was allowed to cool to70° C. and then homogenized at high speed for three minutes. Followinghomogenization, the mixture was allowed to cool to 45-50° C. whilestirring at slow speed with an anchor-type blade. At 45-50° C. themixture was discharged to an appropriate container for storage.

The pH of the resulting formulation was 4.27 and the Brookfieldviscosity (RVT (D), helipath spindle T-C, 10 rpm) was 69,600 cP at roomtemperature (about 21° C.).

Examples 9 and 10: Natural Hair Conditioner Bars

Table 5 shows the relative amounts of ingredients used in the followingexemplary formulations of hair conditioner bars.

TABLE 5 Formula Wt % Ingredient— Trade Name (as supplied) INCI Name(Supplier) Ex 9 Ex 10 Brassica Alcohol Example 1  90.00  20.00 (and)(INOLEX) Brassicyl Valinate Esylate (and) Calcium Gluconate CocosNucifera Virgin Coconut  3.00  2.00 (Coconut) Oil Oil (Anjou)Butyrospermum Cetiol SB45  3.00 — Parkii (BASF) (Shea) Butter DiheptylSuccinate LexFeel N5  1.00  2.00 (and) Capryloyl (INOLEX)Glycerin/Sebacic Acid Copolymer Cetyl Alcohol Cetyl Alcohol, NF —  47.00Tapioca Starch Organic Tapioca —  15.00 Natural (AGRANA) GlycerinGlycerin, USP  1.00  2.00 Caprylyl Glycol Lexgard O  1.00  1.00 (INOLEX)Decyl Glucoside Plantaren 2000 N —  5.00 UP (BASF) Polyglyceryl-4 NikkolTetraglyn —  5.00 Oleate 1-OV (Nikko) Fragrance Oil, Sea Island  1.00 1.00 Cotton BBW (Lebermuth) 100.00 100.00

Examples 9 and 10 were prepared by the “melt and pour” process known tothose skilled in the art. The ingredients were charged to anappropriately sized beaker and heated to 80-85° C. while mixing atmedium speed to maintain uniform dispersion of the buffering agent inthe mixture. The fragrance was withheld from the mixture until the final1-2 minutes of mixing. Following fragrance addition, the mixture wasimmediately discharged to cooled bar molds and cooled rapidly tomaintain a uniform, homogenous solid form. The pH values of a 10%solution of the bar compositions in water were 4.09 and 5.39 for Example9 and Example 10, respectively.

Example 11 and Comparative Example 11—Therapeutic Lotion Formulas

Table 6 shows the relative amounts of ingredients used in theformulations of therapeutic lotion formulas of Example 11 andComparative Example 11. The elucidated viscosity and pH of eachformulation are also shown in Table 6.

TABLE 6 Formula Wt % (as supplied) Comp Ingredient— Trade Name ExampleExample INCI Name (Supplier) 11 10 Water Deionized Water  70.82  71.74Sodium Chloride Sodium Chloride  0.01  0.01 (Morton) Glycerin Glycerin 12.00  12.00 Colloidal Oatmeal AVEENO ®  1.00  1.00 Oatmeal Bath(Johnson & Johnson) Brassicyl Valinate Example 3  6.92 — Esylate (and)(INOLEX) Brassica Alcohol (and) Brassica Glycerides (and) CalciumGluconate Brassicyl Valinate Comparative —  6.00 Esylate (and) Example 3Brassica Alcohol (INOLEX) (and) Brassica Glycerides Isopropyl PalmitateLexol IPP  3.00  3.00 (INOLEX) Petrolatum Vaseline ® Jelly  4.00  4.00(Unilever) Dimethicone XIAMETER ™  1.25  1.25 PMX-200 Silicone Fluid 20cSt (Dow) Caprylhydroxamic Benzostat ™  1.00  1.00 Acid (and) Benzyl(INOLEX) Alcohol (and) Glycerin TOTAL 100.00 100.00 pH  4.19  2.73viscosity 12,400     5,400    

Example 11

To an appropriately sized beaker equipped with overhead mechanicalstirrer and propeller blade and hotplate for heating was charged water,sodium chloride, and glycerin. Mixing was started at medium speed andheating started to bring batch temperature to 80-85° C. Colloidaloatmeal was slowly sifted into the batch and mixed until uniformlydispersed with no appearance of lumps.

When the temperature reached 60-65° C., the self-neutralizing AABC ofExample 3 was added along with isopropyl palmitate, petrolatum, anddimethicone. Upon reaching 80-85° C., the batch was mixed at medium-highspeed for 10-15 minutes to ensure all ingredients were melted anduniformly dispersed. Heating was stopped and the batch allowed to coolto ca. 70° C. with continued mixing. At 70° C., the batch washomogenized at 3000 rpm for three minutes and then mixing was resumed atlow-medium speed while allowing to cool. Once the batch temperaturecooled to 55° C., caprylhydroxamic acid (and) benzyl alcohol (and)glycerin were added. The mixture was allowed to cool to 40-45° C. whilestirring at slow speed with an anchor-type blade.

At ca. 40° C., the mixture was discharged to an appropriate containerfor storage. The pH of the resulting formulation was 4.19 and theBrookfield viscosity (RVT (D), helipath spindle T-C, 10 rpm) was 12,400cP at room temperature (about 21° C.).

Comparative Example 11

Comparative Example 11 was prepared using Comparative Example 3, a nonself-neutralizing AABC composition, according to the same process asExample 11. The resulting lotion exhibited an undesirably low pH value(2.73) and an undesirably low viscosity (5,400 cP) compared to Example11.

Example 12 and Comparative Example 12—High Emollient Skin Cream

Table 7 shows the relative amounts of ingredients used in theformulations Example 12 and Comparative Example 12. The elucidatedviscosity and pH of each formulation are also shown in Table 7.

TABLE 7 Formula Wt % (as supplied) Comp Ingredient— Trade Name ExampleExample INCI Name (Supplier) 12 12 Main Batch (Water Phase) WaterDeionized Water  62.48  64.01 Caprylhydroxamic Spectrastat ™  1.00  1.00Acid (and) Glyceryl G2 (INOLEX) Caprylate (and) Glycerin Oil PhaseBrassicyl Valinate Example 3  11.53 — Esylate (INOLEX) (and) BrassicaAlcohol (and) Brassica Glycerides (and) Calcium Gluconate BrassicylValinate Comparative —  10.00 Esylate Example 3 (and) Brassica (INOLEX)Alcohol (and) Brassica Glycerides Helianthus Annus Sunflower  8.33  8.33(Sunflower) Seed Oil Seed Oil Caprylic/Capric Lexol ™ GT-865  8.33  8.33Triglyceride (INOLEX) Isopropyl Palmitate Lexol ™ IPP  8.33  8.33(INOLEX) TOTAL 100.00 100.00 pH  4.16  2.55 viscosity 69,400    21,800    

Example 12

In an appropriately sized beaker equipped with overhead mechanicalstirrer and propeller blade and hotplate for heating, an oil phase wasprepared by combining Helianthus Annus (sunflower) seed oil,caprylic/capric triglyceride, and isopropyl palmitate. The mixture washeated to 75-80° C. while mixing at low-medium speed. While heating, theself-neutralizing AABC composition of Example 3 was added and the oilphase mixed until uniform.

The oil phase was held at 75-80° C. with mixing to maintain a uniformdispersion without sedimentation. In a separate beaker equipped withequipped with overhead mechanical stirrer and propeller blade andhotplate for heating, water and caprylhydroxamic acid (and) glycerylcaprylate (and) glycerin were combined and heated to 75-80° C. whilemixing at low-medium speed. At 75-80° C., mixing speed was increased tomedium-high and the hot oil phase was added to the main batch andallowed to mix at 75-80° C. until uniform.

Heating was stopped and the batch was allowed to cool to ca. 70° C. andthen homogenized at 3000 rpm for three minutes. Mixing was resumed atlow-medium speed with an anchor-type bladed while allowing to cool. Oncethe batch temperature cooled to ca. 45-50° C., the mixture wasdischarged to an appropriate container for storage. The pH of theresulting formulation was 4.16 and the Brookfield viscosity (RVT (D),heilapath spindle T-C, 10 rpm) was 69,400 cP at room temperature (about21° C.).

Comparative Example 12

Comparative Examples 12 was prepared using Comparative Example 3, anonself-neutralizing AABC composition, according to the same process asExample 12. The resulting cream exhibited an undesirably low pH value(2.55) and an undesirably low viscosity (21,800 cP) compared to Example12.

Example 13—Natural Shave Lotion

Example 13 was prepared according to the same general proceduredescribed in Example 12. Citrus Aurantium Dulcis (orange) peel oil andfragrance were post-added to the batch during the cooling period whenthe temperature had cooled to <55° C. The pH of the resultingformulation was 4.03 and the Brookfield viscosity (RVT (D), helipathspindle T-C, 10 rpm) was 50,400 cP at room temperature (about 21° C.).

Table 8 shows the ingredients and their relative amounts as used forExample 13.

TABLE 8 Formula Wt % Ingredient— Trade Name (as supplied) INCI Name(Supplier) Ex 13 Water Phase Deionized Water Deionized 75.32 WaterGlycerin Glycerin 3.00 Caprylhydroxamic Acid (and) Spectrastat ™ 1.00Glyceryl Caprylate (and) Glycerin (INOLEX) Oil Phase Brassicyl ValinateEsylate (and) Example 3 10.38 Brassica Alcohol (and) Brassica (INOLEX)Glycerides (and) Calcium Gluconate Triheptanoin (and) C13-15 AlkaneLexFeel ™ 4.00 WOW-A (INOLEX) Diheptyl Succinate (and) CaprylylLexFeel ™ 4.00 Glycerin/Sebacic Acid Copolymer N100 (INOLEX) SimmondsiaChinensis (Jojoba) Jojoba Oil 2.00 Seed Oil (Now Solutions) Post AddsCitrus Aurantium Dulcis (Orange) Orange Peel Oil 0.15 Peel Oil (NowSolutions) Fragrance Oil, Euc/ 0.15 Spearmint BBW Type (Lebermuth Co.)TOTAL 100.00

Where applicable, chemicals are specified by their INCI Name accordingto the guidelines of the International Nomenclature of CosmeticIngredients. Additional information, including suppliers and tradenames, can be found under the appropriate INCI monograph in theInternational Cosmetic Ingredient Dictionary and Handbook, 16th Editionpublished by the Personal Care Products Council, Washington, D.C., oronline in the Personal Care Products Council On-Line INFOBASE(http://online.personalcarecouncil.org).

It will be appreciated by those skilled in the art that changes could bemade to the embodiments described above without departing from the broadinventive concept thereof. It is understood, therefore, that thisinvention is not limited to the particular embodiments disclosed, but itis intended to cover modifications within the spirit and scope of thepresent invention as defined by the appended claims.

What is claimed is:
 1. A self-neutralizing amino acid-based cationiccomposition comprising an AABC, a nonionic amphiphile, and an anhydrousbuffering agent.
 2. The composition of claim 1 wherein when thecomposition is dispersed or dissolved in an aqueous solvent, theresultant solution/dispersion has a pH of greater than about
 4. 3. Thecomposition of claim 1, wherein the AABC is the reaction product of anamino acid having a non-polar side chain wherein the amine group of theamino acid has been neutralized with an acid; with (ii) a long chainfatty alcohol.
 4. The composition of claim 3 wherein the neutralizingacid is ethanesulfonic acid.
 5. The composition of claim 3 wherein theamino acid is selected from L-alanine, L-valine, L-leucine,L-isoleucine, and/or mixtures of the same, and the fatty alcohol isselected from coconut oil, stearyl alcohol, isostearyl alcohol,brassicyl alcohol and mixtures thereof.
 6. The composition of claim 1,wherein the AABC is selected from brassicyl valinate esylate, cetylvalinate esylate, cetearyl valinate esylate, stearyl valinate esylate,isostearyl valinate esylate, behenyl valinate esylate, octyldodecylvalinate esylate, decyltetradecyl valinate esylate; brassicylisoleucinate esylate, cetyl isoleucinate esylate, cetearyl isoleucinateesylate, stearyl isoleucinate esylate, isostearyl isoleucinate esylate,behenyl isoleucinate esylate, octyldodecyl isoleucinate esylate,decyltetradecyl isoleucinate esylate, brassicyl valinate esylate,brassicyl isoleucinate esylate and mixtures thereof.
 7. The compositionof claim 1, wherein the non-nonionic amphiphile is selected from a fattyalcohol, a fatty glyceryl ester, fatty glycol esters, fatty esters ofpolyglycerol, fatty esters of methyl glucose, fatty esters of sorbitanand mixtures thereof.
 8. The composition of claim 7, wherein thenon-nonionic amphiphile has about 10 to about 35 carbon atoms.
 9. Thecomposition of claim 1, wherein the non-nonionic amphiphile is brassicaalcohol and the AABC is selected from brassicyl valinate esylate andbrassicyl isoleucinate esylate.
 10. The composition of claim 1, whereinthe anhydrous buffering agent is selected from an alkali metal salt ofgluconic acid and mixtures thereof.
 11. The composition of claim 1,wherein the composition is in anhydrous solid form.
 12. A method ofpreparing a self-neutralizing amino acid-based cationic compositioncomprising combining an AABC, a nonionic amphiphile and an anhydrousbuffering agent, wherein the resulting composition is in an anhydroussolid form.
 13. The method of claim 12, wherein the AABC is the reactionproduct of an amino acid having a non-polar side chain wherein the aminegroup of the amino acid has been neutralized with an acid; with (ii) along chain fatty alcohol.
 14. The method of claim 13, wherein the aminoacid is selected from L-alanine, L-valine, L-leucine, L-isoleucine,and/or mixtures of the same, and the fatty alcohol is selected fromcoconut oil, stearyl alcohol, isostearyl alcohol, brassicyl alcohol andmixtures thereof.
 15. The method of claim 12, wherein the AABC isselected from brassicyl valinate esylate, cetyl valinate esylate,cetearyl valinate esylate, stearyl valinate esylate, isostearyl valinateesylate, behenyl valinate esylate, octyldodecyl valinate esylate,decyltetradecyl valinate esylate; brassicyl isoleucinate esylate, cetylisoleucinate esylate, cetearyl isoleucinate esylate, stearylisoleucinate esylate, isostearyl isoleucinate esylate, behenylisoleucinate esylate, octyldodecyl isoleucinate esylate, decyltetradecylisoleucinate esylate and mixtures thereof.
 16. The method of claim 12,wherein the AABC is selected from brassicyl valinate esylate, brassicylisoleucinate esylate and mixtures thereof.
 17. The method of claim 12,wherein the non-nonionic amphiphile is selected from a fatty alcohol, afatty glyceryl ester, fatty glycol esters, fatty esters of polyglycerol,fatty esters of methyl glucose, fatty esters of sorbitan and mixturesthereof.
 18. The method of claim 12, wherein the non-nonionic amphiphileis brassica alcohol and the AABC is selected from brassicyl valinateesylate and brassicyl isolecinate esylate.
 19. The method of claim 12wherein the anhydrous buffering agent is selected from an alkali metalsalt of gluconic acid, an alkaline earth metal salt of gluconic acid andmixtures thereof.
 20. A formulation comprising the self-neutralizingAABC composition of claim 1 and at least one additive.
 21. Theformulation of claim 20 wherein the additive is selected from water,emollients, humectants, conditioning agents, chelating agents, pHadjusting agents, fragrance, colorant, exfoliating agents, antioxidants,silica, plant extracts, surfactants, and mixtures thereof.